Acetylthiomethyl-diphenylphosphine borane complex

Base Information

Chemical Name:Acetylthiomethyl-diphenylphosphine borane complex
CAS No.:446822-71-5
Molecular Formula:C15H18BOPS
Molecular Weight:288.158
Hs Code.:
European Community (EC) Number:625-039-6
DSSTox Substance ID:DTXSID10460631
Mol file:446822-71-5.mol

Synonyms:446822-71-5;CID 11266195;Acetylthiomethyl-diphenylphosphine borane complex;AGN-PC-005LSK;SCHEMBL4848056;DTXSID10460631;MXPNVFCCEGQGEN-UHFFFAOYSA-N;Borane Thioacetic Acid S-[(Diphenylphosphanyl)-Methyl] Ester

Suppliers and Price of Acetylthiomethyl-diphenylphosphine borane complex

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Sigma-Aldrich
Acetylthiomethyl-diphenylphosphine borane complex ≥98.0%
250mg
$ 158.00

Sigma-Aldrich
Acetylthiomethyl-diphenylphosphine borane complex ≥98.0%
1g
$ 565.00

American Custom Chemicals Corporation
ACETYLTHIOMETHYL-DIPHENYLPHOSPHINE BORANE COMPLEX 95.00%
5MG
$ 496.09

Total 5 raw suppliers

Chemical Property of Acetylthiomethyl-diphenylphosphine borane complex

Chemical Property:

Melting Point:52-55 °C
PSA：55.96000
LogP:2.17260
Storage Temp.:2-8°C
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:5
Exact Mass:285.0674284
Heavy Atom Count:19
Complexity:239

Purity/Quality:

99% ^*data from raw suppliers

Acetylthiomethyl-diphenylphosphine borane complex ≥98.0% ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:Xi
Statements: 36/37/38
Safety Statements: 26

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:[B].CC(=O)SCP(C1=CC=CC=C1)C2=CC=CC=C2
Uses Traceless Staudinger ligation reagent with borane protecting group. The borane group stabilizes the phosphine against oxidation and can be easily removed with mild basic or acidic conditions to yield the active phosphine. After reaction with an azide, the phosphine is eliminated in the presence of water to yield a native amide bond. Used in the synthesis of cyclic peptides. Traceless Staudinger ligation reagent with borane protecting group. The borane group stabilizes the phosphine against oxidation and can be easily removed with mild basic or acidic conditions to yield the active phosphine. After reaction with an azide, the phosphine is eliminated in the presence of water to yield a native amide bond.Used in the synthesis of cyclic peptides.

Technology Process of Acetylthiomethyl-diphenylphosphine borane complex

There total 6 articles about Acetylthiomethyl-diphenylphosphine borane complex which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

: 815577-64-1
(borane)diphenylphosphinomethyl sulfonate

: 507-09-5
tiolacetic acid

: 446822-71-5
(borane)diphenylphosphinomethanethiol acetate

Guidance literature:: With caesium carbonate; In N,N-dimethyl-formamide; at -20 - 20 ℃; for 8h;
DOI:10.1021/ol048271s

Reference yield: 65.0%

: 815577-64-1
(borane)diphenylphosphinomethyl sulfonate

: 10387-40-3
potassium thioacetate

: 446822-71-5
(borane)diphenylphosphinomethanethiol acetate

Guidance literature:: In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;
DOI:10.1002/anie.201611415

Reference yield:

: 127686-81-1
hydroxymethyl(diphenyl)phosphine borane complex

: 446822-71-5
(borane)diphenylphosphinomethanethiol acetate

Guidance literature:: Multi-step reaction with 2 steps

1: 78 percent / Et₃N / CH₂Cl₂ / 15 h / 0 °C

2: 65 percent / Cs₂CO₃ / dimethylformamide / 8 h / -20 - 20 °C

With caesium carbonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol048271s